Flippin–Lodge angle

The Flippin–Lodge angle is one of two angles used by organic and biological chemists studying the relationship between a molecule's chemical structure and ways that it reacts, for reactions involving "attack" of an electron-rich reacting species, the nucleophile, on an electron-poor reacting species, the electrophile. Specifically, the angles—the Bürgi–Dunitz, , and the Flippin–Lodge, —describe the "trajectory" or "angle of attack" of the nucleophile as it approaches the electrophile, in particular when the latter is planar in shape. This is called a nucleophilic addition reaction and it plays a central role in the biological chemistry taking place in many biosyntheses in nature, and is a central "tool" in the reaction toolkit of modern organic chemistry, e.g., to construct new molecules such as pharmaceuticals. Theory and use of these angles falls into the areas of synthetic and physical organic chemistry, which deals with chemical structure and reaction mechanism, and within a sub-specialty called structure correlation. Because chemical reactions take place in three dimensions, their quantitative description is, in part, a geometry problem. Two angles, first the Bürgi–Dunitz angle, , and later the Flippin–Lodge angle, , were developed to describe the approach of the reactive atom of a nucleophile (a point off of a plane) to the reactive atom of an electrophile (a point on a plane). The is an angle that estimates the displacement of the nucleophile, at its elevation, toward or away from the particular R and R' substituents attached to the electrophilic atom (see image). The is the angle between the approach vector connecting these two atoms and the plane containing the electrophile (see the Bürgi–Dunitz article). Reactions addressed using these angle concepts use nucleophiles ranging from single atoms (e.g., chloride anion, Cl–) and polar organic functional groups (e.g., primary amines, R"-NH2), to complex chiral catalyst reaction systems and enzyme active sites.